Chris Pressley defeated Oren Motevassel 6-2 7-6 in the USA 4 Masters 4 qualifying round on hard. The upset overturned the form book — Oren Motevassel came in leading the head-to-head 2–0, but Chris Pressley had been the form player, winning 6 of their last 10 on hard. Chris Pressley claimed a first win over Oren Motevassel in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-09-06 | USA 5 Masters 4 | F | hard | Oren Motevassel | 5-7 6-2 6-0 |
| 1995-07-07 | USA 4 Masters 1 | R16 | hard | Oren Motevassel | 6-3 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.